Structure of H-D-Phe(2-F)-OH
CAS No.: 97731-02-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: (R)-2-Amino-3-(2-fluorophenyl)propanoic acid
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CAS No. : | 97731-02-7 |
Formula : | C9H10FNO2 |
M.W : | 183.18 |
SMILES Code : | [H][C@@](N)(CC1=C(F)C=CC=C1)C(O)=O |
Synonyms : |
(R)-2-Amino-3-(2-fluorophenyl)propanoic acid
|
MDL No. : | MFCD00066447 |
InChI Key : | NYCRCTMDYITATC-MRVPVSSYSA-N |
Pubchem ID : | 716322 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 45.46 |
TPSA ? Topological Polar Surface Area: Calculated from |
63.32 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.15 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-1.31 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.2 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.69 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.29 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.33 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.29 |
Solubility | 93.1 mg/ml ; 0.508 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
0.48 |
Solubility | 551.0 mg/ml ; 3.01 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.15 |
Solubility | 1.31 mg/ml ; 0.00716 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-8.35 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.94 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phenylalanine ammonia-lyase from Pseudozyma antarctica yeast; In aq. buffer; at 30℃; for 168h;pH 8.5;Resolution of racemate; | General procedure: The ammonia elimination reaction mixtures containing 5mM of theracemic phenylalanines (rac-1a-s) in 100mM TRIS buffer (pH 8.5) andpurified PzaPAL or PcPAL (50 Xg, either) in 1 mL reaction volume wereincubated at 30 C. Samples (50 XL) taken at different time points (17,40, 64, and 168 h) from the reaction mixtures were analyzed by HPLCfor conversion and ee values, using previously developed methods [44].The ammonia addition and elimination reactions were followed byHPLC measurements. Conversions were determined on Agilent 1200HPLC instrument using Phenomenex Gemini NX-C-18 column and amixture of NH4OH buffer (0.1 M, pH 8.5) and MeOH at a flow rate of1 mL min-1. Conversions were calculated from peak area integrationswith use of appropriate response factor (Table S2). Enantiomer separationswere carried out on Agilent 1100 HPLC instrument usingCrownpak CR-I (+) column and a mixture of aqueous HClO4, pH 1.5and acetonitrile as eluent at a flow rate of 0.4 mL min-1. (Table S3). |
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